POLYMERS AND PLASTICS

Date: Name : _________________________

Partner : _________________________
TA : _________________________
Section : B ___
A. POLYESTERS
(i) DEPOLYMERISATION
Balanced reaction equation:

PROCEDURE
RESULTS
Yield of terephthalic acid / g =
Molecular weight of terephthalic acid / g mol -1 =
Yield of terephthalic acid / moles =
Initial mass of PET / g =
Unreacted mass of PET /g =
Mass of PET reacted / g =
Molecular weight of the PET repeating unit / g mol -1 =
Theoretical moles of terephthalic acid formed / moles =
% Yield of terephthalic acid =

DISCUSSION:

CONCLUSIONS:
 CHEM 353_PP.3

MECHANISMS:
(a) Draw a curly arrow mechanism for the base promoted saponification of the PETE plastic
to form the terephthalic acid product.

(b) Ester hydrolysis can also be acid catalysed. Draw a curly arrow mechanism for the acid
catalysed hydrolysis (using H+ / H2O) of the PET plastic to form the terephthalic acid
product.
 CHEM 353_PP.4

B. POLYAMIDE
Observations during Preparation of Nylon

C. QUESTIONS
Answer the following questions related to the chemistry of polymers experiment :
(a) What functional groups are present in (i) PET, (ii) Nylon and (iii) adipoyl chloride ?

(b) These three functional groups in question 1(a) are part of a larger family of functional
groups. What is that larger family ?

(c) The larger family of functional groups in question 1(b) typically undergo reactions of a
common general mechanistic pathway. The hydrolysis of PETE and the formation of Nylon in
this experiment are both examples of this. What is the name of type of mechanism ?

(d) Industrially, nylon-6,6 is made by heating a diamine with a dicarboxylic acid. In a

laboratory setting, it is difficult to make nylon using this method due to the formation of another
product. Provide an equation to show the reaction that forms the other product.
CHEM 353_PP.5